Homes for Sale Near Kissimmee Middle in Kissimmee - 283 homes

Remarks: This beautifully maintained first-floor three-bedroom, two-bathroom condo in Kissimmee offers an exceptional opportunity for homeowners and investors alike. Conveniently located near major shopping centers, restaurants, and entertainment, and just minutes from Walt Disney World Resort, this property combines comfort, convenience, and lifestyle. Situated within a secure gated community, residents enjoy peace of mind along with amenities designed for relaxation and enjoyment. The community features elevator access to all floors and a beautifully designed resort-style pool overlooking the lake, creating the perfect setting to unwind. Located on the first floor for added convenience and easy access, this condo is ideal for families, professionals, or investors seeking strong rental potential in one of Central Florida’s most desirable areas.

Listing is courtesy of: ALTIS REALTY (407-401-7447)

Listing Agent: Reynaldo Izaguirre, Pa (407-683-0998)

Remarks: Prime location in the heart of Kissimmee’s tourist corridor. This property at 2909 Theme St, located in Reflections at Storey Lake, is just minutes from US-192, Disney, and Orlando’s top attractions, with immediate access to restaurants, shopping centers, supermarkets, and entertainment. This is one of the most desirable areas for both homeowners and long-term rental investors due to its high and consistent demand. The townhome is practically like new. Featuring 3 bedrooms, 2.5 bathrooms, and a 2-car garage, it offers a modern open-concept design and has been exceptionally well maintained, making it truly move-in ready with no renovations needed. Enjoy resort-style community amenities, and as an added bonus, the HOA covers Spectrum Internet and TV. Furniture is negotiable, making this an ideal opportunity whether you’re looking for a primary residence or a turnkey investment property ready to generate income. Prime location + like-new condition + strong rental demand = a smart investment. ?? Schedule your private showing today.

Listing is courtesy of: MY REALTY GROUP, LLC. (786-847-7421)

Listing Agent: Esther Atencio (321-314-9374)

Remarks: PRICE IMPROVEMENT! LOCATION LOCATION LOCATION!! Top Orlando attractions! Stay close to Disney, Universal Parks, Outlets, I-Drive. TURNKEY INVESTMENT OPPORTUNITY! Welcome to this high demand SEVEN DWARFS CONDO 24-7 GUARD GATED COMMUNITY offers RESORT STYLE amenities, included: tennis and basketball courts, beach-tennis, large community pool and spa, playground, club house, game room, fitness center, Tiki Bar, picinic areas, paddle-boats, scenic walking areas, car wash, and lots of spaces to relaxing. This beautiful and well maintained townhouse included a living and dining combo area, fully equipped modern kitchen, washer and dryer combo, 3 spacious bedrooms (PRIMARY BEDROOM DOWNSTAIRS) and 2 full bath. NEW A/C, NEW dryer and washer, NEW fridge, NEW stove. Community is zoned for SHORT-TERM vacation rentals, LONG-TERM rentals, or even as your PRIMARY residence. STRESS FREE: HOA FEE COVERS master building insurance, exterior painting and maintenance, cable, internet, pest control, roof, and common areas. THAT IS THE HOUSE YOU ARE LOOKING FOR! Available FULLY FURNISHED! Start generating income immediately! Schedule your visit today!

Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)

Listing Agent: Vania Machado (321-333-9290)

Remarks: Exceptional opportunity in Storey Lake! This well-maintained 4-bedroom, 3-bathroom home features a private pool and a highly desirable open-concept layout, ideal for both personal use and investment purposes. The property offers themed bedrooms, adding strong appeal for short-term rental potential in a prime vacation community. The spacious living and dining areas flow seamlessly into a fully equipped kitchen, creating a functional and inviting environment. The floor plan includes a first-floor queen bedroom, an upstairs king-size primary suite, and additional bedrooms designed to maximize occupancy. Located just minutes from major attractions, shopping, and dining, Storey Lake is a sought-after resort-style community known for its amenities and strong rental demand. This property presents an excellent opportunity for buyers seeking a primary residence, vacation home, or income-producing asset.

Listing is courtesy of: GLASSTONE GROUP INC (321-988-4663)

Listing Agent: Barbara Cunha De Freitas (617-458-0838)

Remarks: Welcome to 2135 Water Mania Ct, a beautifully maintained fully furnished 2-bedroom, 2-bath townhouse located in the highly desirable Fantasy World Resort. This spacious two-story villa offers an open-concept layout with comfortable living and dining areas, a fully equipped kitchen, living room with sofa-bed and a screened patio perfect for relaxing after a day at the parks. The home features stylish furnishings, washer and dryer, ample parking, and resort-style living just minutes from Walt Disney World, shopping, dining, and major attractions. Ideal as a primary residence, second home, vacation home, or short-term rental investment, the community offers exceptional amenities including a lazy river, water slides, resort-style pools, splash pad, fitness center, tennis courts, mini golf, playground, and 24-hour security. Enjoy the perfect combination of comfort, convenience, and income-producing potential in the heart of Kissimmee.

Listing is courtesy of: RE/MAX SELECT GROUP (321-939-3004)

Listing Agent: Ivette Rico, Pll (407-558-9636)

Remarks: Brand New Interior Paint--Move in Ready! Welcome to the beautifully maintained 3 Bedroom 2-Bathroom home located in the desirable gated community of Cypress Reserve! Featuring an open concept layout with wood flooring throughout, crown molding and window treatments! This home offers both style and comfort on a gorgeous, oversized lot! The kitchen is fully equipped with a refrigerator, dishwasher, oven and microwave and showcases Corian countertops, tiled backsplash, maple cabinetry, and a closet pantry. An eat-in area just off of the family room creates the perfect space for casual dining and everyday living. The spacious primary suite and secondary bedrooms offer a functional split floor plan. A 2023 AC and 2018 ROOF provides a peace of mind. Washer and dryer convey with the sale. Step outside and enjoy a large, enclosed lanai overlooking an expansive backyard--ideal for entertaining or relaxing year-round. Move in ready and conveniently located near shopping (The Loop), dining, and major roadways. Come and see this home today!

Listing is courtesy of: BHHS FLORIDA REALTY (407-876-2090)

Listing Agent: Catherine Lambert Pa (407-908-2525)

Remarks: Turnkey, fully furnished 4-bedroom, 3-bathroom vacation townhome in the highly sought-after Regal Oaks Resort—one of the closest short-term rental communities to Walt Disney World Resort! Located in the heart of Kissimmee near Orlando’s top attractions, this income-producing property is ideal for Airbnb, VRBO, or personal use. Designed with both guests and owners in mind, this home features an open-concept layout with durable wood-look flooring, a bright kitchen with granite countertops, and a spacious living and dining area perfect for entertaining. The layout comfortably accommodates larger groups, making it highly desirable for vacation rentals in the Disney/Orlando market. A standout feature of this property is its professionally themed, Disney-inspired interior, creating a memorable guest experience that drives strong reviews and repeat bookings. The main level includes a bedroom and full bathroom, offering convenience and flexibility for multi-generational guests. Upstairs, the private primary suite provides a relaxing retreat, while additional themed bedrooms continue to elevate the home’s rental appeal in a competitive short-term rental market. Step outside to your private screened-in patio with hot tub, a premium amenity that enhances guest satisfaction and booking potential year-round. Located just minutes from Old Town Kissimmee and a short drive to Universal Orlando Resort and SeaWorld Orlando, this property offers unbeatable access to Central Florida’s most visited destinations, shopping, dining, and Orlando International Airport. Regal Oaks Resort amenities include a gated entrance, lakefront pool with water slides, fitness center, tennis courts, and on-site dining—making this one of the most desirable vacation rental communities in Kissimmee near Disney. Fully turnkey and has DOZENS OF BOOKINGS ALREADY IN PLACE THROUGHOUT 2026 AND BEYOND!—this is a rare opportunity to own a high-demand short-term rental in the Disney area with proven guest appeal.

Listing is courtesy of: ERA GRIZZARD REAL ESTATE (407-203-5800)

Listing Agent: Shawn Mccormick (321-439-4277)

Remarks: INVESTOR OPPORTUNITY! HIGH INCOME POTENTIAL — PERFECT FOR VRBO / AIRBNB / SHORT-TERM RENTAL! DAILY RENTALS ALLOWED! Prime location in Kissimmee just minutes from Disney parks, premium shopping, restaurants, entertainment, and major attractions. Excellent CASH FLOW potential in one of Central Florida’s most desirable vacation rental areas!

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Lorenzino Salerno (407-452-7940)

Remarks: INVESTOR OPPORTUNITY! HIGH INCOME POTENTIAL — PERFECT FOR VRBO / AIRBNB / SHORT-TERM RENTAL! DAILY RENTALS ALLOWED! Prime location in Kissimmee just minutes from Disney parks, premium shopping, restaurants, entertainment, and major attractions. Excellent CASH FLOW potential in one of Central Florida’s most desirable vacation rental areas!

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Lorenzino Salerno (407-452-7940)

Remarks: Under contract-accepting backup offers. INVESTOR OPPORTUNITY! HIGH INCOME POTENTIAL — PERFECT FOR VRBO / AIRBNB / SHORT-TERM RENTAL! DAILY RENTALS ALLOWED! Prime location in Kissimmee just minutes from Disney parks, premium shopping, restaurants, entertainment, and major attractions. Excellent CASH FLOW potential in one of Central Florida’s most desirable vacation rental areas!

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Lorenzino Salerno (407-452-7940)

Remarks: ?? INVESTOR OPPORTUNITY! ?? HIGH INCOME POTENTIAL — PERFECT FOR VRBO / AIRBNB / SHORT-TERM RENTAL! DAILY RENTALS ALLOWED! Prime location in Kissimmee just minutes from Disney parks, premium shopping, restaurants, entertainment, and major attractions. Excellent CASH FLOW potential in one of Central Florida’s most desirable vacation rental areas!

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Lorenzino Salerno (407-452-7940)

Remarks: ?? INVESTOR OPPORTUNITY! ?? HIGH INCOME POTENTIAL — PERFECT FOR VRBO / AIRBNB / SHORT-TERM RENTAL! DAILY RENTALS ALLOWED! Prime location in Kissimmee just minutes from Disney parks, premium shopping, restaurants, entertainment, and major attractions. Excellent CASH FLOW potential in one of Central Florida’s most desirable vacation rental areas!

Listing is courtesy of: AGENT TRUST REALTY CORPORATION (407-251-0669)

Listing Agent: Lorenzino Salerno (407-452-7940)

Remarks: INCOME PRODUCING ASSET! Just discontinued from a successful property management program due to limited showing availability while fully booked, this is your opportunity to own a FRESHLY REMODELED, FULLY FURNISHED 6-BEDROOM, 6.5-BATH luxury residence OFFERED BELOW APPRAISED VALUE. Whether you are searching for a PRIMARY RESIDENCE, SECOND HOME, or a HIGH-PERFORMING SHORT-TERM RENTAL INVESTMENT, this property offers exceptional versatility in one of Central Florida’s MOST SOUGHT-AFTER RESORT COMMUNITIES. Step inside to discover an OPEN-CONCEPT floor plan featuring a GOURMET KITCHEN with stainless steel appliances, an expansive family room, and a spacious upstairs great room ideal for entertainment and gatherings. Outdoors, enjoy your PRIVATE SCREENED AND HEATED POOL, creating the perfect setting for year-round relaxation or hosting guests. Ideally located just minutes from DISNEY THEME PARKS, The Loop, Medieval Times, and Gatorland, this home combines RESORT-STYLE LIVING with OUTSTANDING INVESTMENT POTENTIAL and long-term appreciation. The HOA includes cable TV, HIGH-SPEED WI-FI, and lawn maintenance, while residents enjoy PREMIUM COMMUNITY AMENITIES including a resort-style pool with cabanas, fitness center, and scenic walking trails. This TURNKEY FLORIDA RETREAT offers the perfect blend of luxury, lifestyle, and value. Schedule your private showing today.

Listing is courtesy of: NOBSKA REAL ESTATE LLC (689-276-1593)

Listing Agent: Laura Teixeira, Pa (941-962-2413)

Remarks: Under contract-accepting backup offers. One of the largest floorplans in Flora Ridge, offering over 1,600 sq ft of flexible living space in a gated community just minutes from The Loop, Osceola Parkway, and under 10 miles to Disney. This 3-bedroom, 2-bath condo is ideally positioned on the 3rd floor with elevator access and features a versatile bonus space off the primary suite—perfect for a home office, nursery, or potential 4th bedroom. The split floorplan creates privacy while still feeling open and functional. Inside, the home has been thoughtfully upgraded with modern finishes throughout. The kitchen stands out with upgraded cabinetry, stainless steel appliances, stone countertops, recessed lighting, and a custom Ambrosia Maple butcher block. Additional upgrades include a remodeled walk-in pantry, laminate flooring throughout, Alexa-enabled smart lighting and thermostat, USB outlets, and a sleek floating entertainment system in the living room. Custom Elfa closet systems and built-in dining banquette seating add both style and storage. Updated with high-performance vinyl replacement windows, featuring durable double-pane glass for improved energy efficiency, insulation, and noise reduction. Standard double-hung design allows for easy operation and maintenance. Step outside to a screened-in balcony, ideal for enjoying fresh air year-round. The unit also includes a ventless washer and dryer, allowing flexibility in placement, along with ceiling fans in every room. The exterior of this community was renovated with new balcony, paint and screens added. Additional highlights include a newer AC, covered parking spaces, and ample guest parking. Offsite security guard access.

Listing is courtesy of: REAL BROKER, LLC (855-450-0442)

Listing Agent: Meagan Waddell (321-945-0008)

Remarks: One or more photo(s) has been virtually staged. Seller is Highly Motivated – Bring All Offers! Welcome to the gated community of Windsor Point, where comfort, convenience, and natural beauty come together. This spacious 3-bedroom, 2-bath residence with a versatile flex room offers a thoughtfully designed layout ideal for both entertaining and everyday living. Upon entering the home, you’re greeted by a welcoming foyer that opens into a bright formal living room—perfect for hosting guests or creating a peaceful sitting area. The split floor plan provides privacy, while the expansive family room serves as the heart of the home, offering plenty of space for gatherings, movie nights, or relaxing after a long day. Sliding glass doors lead to a generously sized backyard, fully enclosed with durable vinyl fencing for privacy and security. Whether you envision weekend barbecues, a play area, space for pets, or a future pool, this yard provides endless possibilities. The home features easy-care ceramic tile flooring throughout—ideal for Florida living. The spacious kitchen is designed for functionality and flow, complete with abundant cabinetry, ample counter space, and an open layout that allows you to stay connected while cooking or entertaining. The flex room can easily function as a home office, workout room, craft room, or homeschool space. Prime Location: Located just 5 minutes from The Loop, featuring upscale shopping, restaurants, and a movie theater. Enjoy quick access to major highways, including Osceola Parkway, John Young Parkway, and the Florida Turnpike, for easy commuting. World-famous attractions such as Disney theme parks, Disney Springs, and Old Town are just 6–10 miles away. Orlando International Airport (MCO) is approximately 15 miles from the property. This home offers space, flexibility, and a highly desirable location within a secure community—making it an excellent opportunity for primary homeowners, second-home buyers, or investors alike. Schedule your private tour today to fully appreciate this home's charm!

Listing is courtesy of: AVANTI WAY REALTY LLC (305-229-1146)

Listing Agent: Tiffany Greer (407-709-0582)

Remarks: Welcome to one of the most compelling luxury investment opportunities in Story Lake—where upscale design, prime location, resort amenities, and exceptional income potential come together to deliver robust returns on investment. Here, ROI meets luxury, making this offering stand out for both personal enjoyment and strategic financial gain. This stunning 7-bedroom residence creates a bold first impression. It sits on a premium lot with no direct rear neighbors and offers a tranquil view of the pond. The property is fully furnished & professionally decorated, completely turnkey and ready for immediate enjoyment or rental. The thoughtfully designed interior features rectangular tile flooring throughout the first floor in the foyer, kitchen, baths, dining & living areas, and laundry room. A well appointed home chef’s kitchen offers grey subway tile backsplash, Extended cabinetry with crown molding, grey stainless steel appliances, a spacious pantry, massive center island, and upgraded pendant lighting. The adjacent dining room is elegantly furnished for entertaining and large group stays. The living room is professionally decorated to impress. It features a stunning polished porcelain tile accent wall behind the TV, high-end furnishings, and large sliding glass doors that open directly to the pool area. The first floor also includes: A guest suite with an adjacent full bath & quartz vanity, A dedicated owner’s storage closet, and a spacious laundry room equipped with a washer & two dryers. The garage has been converted into a game & media room, complete with a media projector & comfortable seating, dedicated split HVAC system, popcorn machine, and video games. Upstairs, you’ll find 6 additional bedrooms & 4 full baths; all professionally decorated with premium themed décor elevating the guest experience. Each bedroom is equipped with its own flatscreen TV, enhancing the experience. The rear primary suite offers a view of the pool & wooded area. It features a luxurious ensuite bath with a soaking tub, a separate walk-in shower, a quartz double vanity, a private water closet, and a big walk-in closet. Second-floor highlights include a Princess-themed room, a Mickey Mouse-themed room, and a Toy Story-themed room. There are also two additional spacious bedrooms at the front of the home, including a second primary suite with double queen beds, dual sinks, & a large walk-in shower. Step outside to your private retreat. Enjoy a heated pool and spa, plus a grill and added seating. Resort-Style Amenities allow Owners & guests to enjoy access to one of the most sought-after amenity packages in the area. Offerings include a resort-style clubhouse & community center, an expansive pool complex with a lazy river, water slides, and a splash pad, outdoor entertainment areas for guests and gatherings, a fitness center, jogging trails, a game room, and a theater. For an additional fee, guests can also enjoy: a Mini golf course, Kayak rentals & lake access, Ice cream shop, and a Full-service bar. In addition, the HOA provides basic lawn maintenance & includes basic cable + high-speed internet. These amenities enhance guest satisfaction, occupancy rates, and overall rental performance. From an investment perspective, this home excels: 7-bedroom capacity maximizes occupancy; water view and no rear neighbors drive premium bookings; high-end themed décor supports stronger nightly rates and guest retention; turnkey condition means immediate income potential.

Listing is courtesy of: CENTURY 21 CARIOTI (407-573-2121)

Listing Agent: David Dorman (407-948-8295)

Remarks: Investor special opportunity at 2460 Summerfield Way in Kissimmee. This 2-story townhouse offers immediate rental income with a tenant already in place paying $1,500 per month on a year-long lease, making it a turnkey addition to any investment portfolio. The property features 2 bedrooms, 2.5 bathrooms, and a functional layout designed for comfortable everyday living. The main level includes the shared living and dining areas, along with a conveniently located kitchen and half bath for guests. Upstairs, both bedrooms offer access to full bathrooms, creating a practical setup for residents, roommates, guests, or even a home office configuration. The patio provides additional usable outdoor space for seating, dining, or relaxing while remaining low maintenance. Investors will appreciate the major system updates already completed, including a new roof in 2024, a water heater that is only 1 year old, and an HVAC system replaced in 2022. These improvements help minimize near-term maintenance concerns and add long-term value to the property. Located in Kissimmee, the home offers convenient access to shopping, dining, schools, parks, major roads, and Central Florida attractions. The neighborhood provides a residential setting with everyday essentials nearby, making it an appealing option for both tenants and long-term investors seeking convenience and steady rental potential.

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE PARKS (407-629-4420)

Listing Agent: Thomas Nickley, Jr (407-629-4420)

Remarks: Beautiful and well-maintained single-family home located in a gated community in the heart of Kissimmee, Florida. This stunning property offers 3 bedrooms, a bonus room, 2 bathrooms, and a spacious 2-car garage. The home features 2 A/C units that are approximately one 1/2 year old, smart thermostats for energy efficiency and comfort, a central vacuum system, and a modern wall-mounted water heater. The interior doors and front door have also been freshly painted, giving the home a clean and updated appearance. Inside, you will find an open floor plan with vaulted ceilings and ceramic tile flooring throughout the home. The spacious family room and dining room combination create the perfect setting for entertaining and everyday living. The open kitchen includes an island with electrical outlets, a range hood, a bar, a wine rack, and stainless steel appliances. The bonus room can easily be used as a nursery, office, guest room, or additional bedroom. The primary bathroom features a double vanity, a walk-in closet, and a separate shower. Skylights provide beautiful natural lighting throughout the bathrooms and living areas. Step outside to your screened patio and enjoy breathtaking pond views with a relaxing fountain backdrop, peacecul outdoor setting perfect for morning coffee or evening relaxation. The backyard is surrounded by beautiful palm views, bringing the best of Florida living right to your backyard. Community amenities include a resort-style pool, basketball courts, a tennis court, a playground, and beautifully maintained common areas. Conveniently located just 15-20 minutes from Disney World, Disney Springs, SeaWorld, Universal Studios, International Drive, Downtown Orlando, and Orlando International Airport. Easy access to the Florida Turnpike, plus proximity to schools, shopping centers, restaurants, and hospitals. Schedule your private showing today and experience everything this beautiful home.

Listing is courtesy of: SIGNATURE BROKERS REALTY LLC (407-595-6820)

Listing Agent: Mickie Rodriguez (407-949-4902)

Remarks: Discover this beautifully upgraded 3-bedroom, 2.5-bath townhome located in one of Central Florida’s most sought-after gated communities. Formerly the builder’s model home, this residence showcases premium finishes throughout, including granite countertops, stainless steel appliances, and elegant wall and ceiling trim details. The open-concept main level offers a seamless flow between the kitchen, dining area, and spacious living room, creating an ideal setting for both everyday living and entertaining. A well-appointed half bath on the first floor adds convenience for guests. Upstairs, the primary suite provides a comfortable retreat with a walk-in closet and an ensuite bathroom featuring dual vanities and quartz countertops. Two additional bedrooms, a full bathroom, and a conveniently located laundry closet complete the second floor. Residents enjoy access to resort-style amenities, including a community pool, fitness center, dog park, playground, and a unique hedge maze. Ideally located just minutes from Walt Disney World, Lake Buena Vista, The Loop, and Orlando International Airport, with easy access to Osceola Parkway, I-4, and SR 417. Shopping, dining, and daily conveniences such as Target are all nearby.

Listing is courtesy of: RATIO REAL ESTATE, LLC (407-674-0460)

Listing Agent: Xiaoyu Su (352-216-1257)

Remarks: Short Sale. Discover the ultimate blend of comfort, convenience, and opportunity with this beautifully designed 4-bedroom, 3.5-bath townhouse in Kissimmee. Featuring a private 1 bed, 1 bath in-law suite with its own entrance, this home is perfect for Airbnb, a vacation retreat, or your primary residence. Located in a 24-hour guard-gated community, you’ll enjoy access to top-notch amenities, including a sparkling pool, parks, playgrounds, tennis and basketball courts, and a beach volleyball area—everything you need for a resort-style lifestyle. The spacious interior boasts an open floor plan, ideal for hosting family and friends. The upstairs master suite offers a private balcony where you can unwind with your morning coffee and take in the serene surroundings. Just minutes from Disney, shopping, and dining, this townhouse is a prime location for both leisure and investment. Whether you’re seeking a profitable rental, a vacation getaway, or your next home, this property is a must-see. Own your slice of paradise today!

Listing is courtesy of: KELLER WILLIAMS REALTY AT THE LAKES (407-566-1800)

Listing Agent: Marcelo Gaitan Estabridis (863-399-5675)